ethyl (2S,3S)-2-O-benzoyl-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate

Base Information

Chemical Name:ethyl (2S,3S)-2-O-benzoyl-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate
CAS No.:114185-08-9
Molecular Formula:C₁₆H₂₀O₆
Molecular Weight:308.331
Hs Code.:

Synonyms:ethyl (2S,3S)-2-O-benzoyl-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of ethyl (2S,3S)-2-O-benzoyl-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate

Chemical Property:

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Technology Process of ethyl (2S,3S)-2-O-benzoyl-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate

There total 1 articles about ethyl (2S,3S)-2-O-benzoyl-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

: 114185-07-8
ethyl (2R)-2-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-2-hydroxyacetate

: 65-85-0,8013-63-6
benzoic acid

: 114185-08-9
ethyl (2S,3S)-2-O-benzoyl-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 24h;
DOI:10.1016/S0957-4166(99)00316-X

Reference yield:

: 114185-08-9
ethyl (2S,3S)-2-O-benzoyl-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate

: [(R)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-oxo-ethyl]-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 92 percent / LiAlH₄ / tetrahydrofuran / 3 h / Heating

2: imidazole / tetrahydrofuran / 3 h / -5 °C

3: Et₃N / CH₂Cl₂ / 1 h / 20 °C

4: NaN₃ / dimethylformamide / 10 h / 95 °C

5: H₂ / 10 percent Pd/C / ethanol / 6 h

6: Et₃N / tetrahydrofuran

7: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

8: oxalyl chloride, DMSO; N,N-diisopropylethyl amine / CH₂Cl₂ / 0.42 h / -63 °C

With 1H-imidazole; lithium aluminium tetrahydride; sodium azide; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: Reduction / 2: silylation / 3: mesylation / 4: Substitution / 5: Hydrogenation / 6: carbobenzoxylation / 7: desilylation / 8: Oxidation;
DOI:10.1016/S0957-4166(99)00316-X

Reference yield:

: 114185-08-9
ethyl (2S,3S)-2-O-benzoyl-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate

: 188923-23-1
N-{(2S)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyethyl}carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 92 percent / LiAlH₄ / tetrahydrofuran / 3 h / Heating

2: imidazole / tetrahydrofuran / 3 h / -5 °C

3: Et₃N / CH₂Cl₂ / 1 h / 20 °C

4: NaN₃ / dimethylformamide / 10 h / 95 °C

5: H₂ / 10 percent Pd/C / ethanol / 6 h

6: Et₃N / tetrahydrofuran

7: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; sodium azide; tetrabutyl ammonium fluoride; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: Reduction / 2: silylation / 3: mesylation / 4: Substitution / 5: Hydrogenation / 6: carbobenzoxylation / 7: desilylation;
DOI:10.1016/S0957-4166(99)00316-X